1,2-Dichloroethane → Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylate

HRID 270152

Reaction equation

HRID 270152 reaction equation
[Si:1]([O:18][CH2:19][C:20](=O)[CH:21](Cl)[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH2:37])=[S:36])=[CH:33][CH:32]=1.ClCCCl.O>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[N:37]=[C:35]([C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:40])([F:29])[F:41])=[CH:39][CH:38]=2)[S:36][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 27348234-(Trifluoromethyl)thiobenzamideHCID 17951839Ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}2-chloro-3-oxobutanoate

Product 1

HCID 17951800Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500ml round-bottom flask equipped with a magnetic stir-bar was mixed ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-chloro-3-oxobutanoate (20.4g, 52.88mmoles, 1eq), 4-trifluoromethylthiobenzamide (12.2g, 59.5mmoles, 1.1eq), 1,2-dichloroethane (150ml, 0.44M) and H2O (3ml). This mixture was refluxed for 12hrs. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2(100ml) and washed with sat. NaHCO3. Once the phases were separated, the organic phase washed with water, brine and dried over Na2SO4. This was then filtered, concentrated in vacuo and purified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes) to yield 20.3g (76%) of the titled compound.

Workup

  1. customTo a 500ml round-bottom flask equipped with a magnetic stir-bar
  2. temperatureThis mixture was refluxed for 12hrs
  3. washwashed with sat. NaHCO3
  4. customOnce the phases were separated
  5. washthe organic phase washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationThis was then filtered
  8. concentrationconcentrated in vacuo
  9. custompurified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c69fbdd2ad324f929bc0c46723c1d169
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Linked notes

Loading…